PL205257B1 - Sposób wytwarzania estrów kwasów tłuszczowych z jednowodorotlenowymi alkoholami alkilowymi oraz sposób wytwarzania paliwa do silników wysokoprężnych - Google Patents
Sposób wytwarzania estrów kwasów tłuszczowych z jednowodorotlenowymi alkoholami alkilowymi oraz sposób wytwarzania paliwa do silników wysokoprężnychInfo
- Publication number
- PL205257B1 PL205257B1 PL352527A PL35252700A PL205257B1 PL 205257 B1 PL205257 B1 PL 205257B1 PL 352527 A PL352527 A PL 352527A PL 35252700 A PL35252700 A PL 35252700A PL 205257 B1 PL205257 B1 PL 205257B1
- Authority
- PL
- Poland
- Prior art keywords
- oil
- fatty acid
- acid esters
- transesterification
- catalyst
- Prior art date
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 59
- 239000000194 fatty acid Substances 0.000 title claims abstract description 59
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 59
- -1 fatty acid esters Chemical class 0.000 title claims abstract description 54
- 125000005233 alkylalcohol group Chemical group 0.000 title claims abstract description 43
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 176
- 239000003921 oil Substances 0.000 claims abstract description 71
- 235000011187 glycerol Nutrition 0.000 claims abstract description 67
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 62
- 239000003054 catalyst Substances 0.000 claims abstract description 47
- 235000021588 free fatty acids Nutrition 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 21
- 238000005191 phase separation Methods 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- 239000007858 starting material Substances 0.000 claims abstract description 10
- 150000001298 alcohols Chemical class 0.000 claims abstract description 8
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 7
- 239000002283 diesel fuel Substances 0.000 claims abstract description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 96
- 235000019198 oils Nutrition 0.000 claims description 68
- 239000003925 fat Substances 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000003626 triacylglycerols Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 150000004703 alkoxides Chemical class 0.000 claims description 6
- 238000009884 interesterification Methods 0.000 claims description 6
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 6
- 150000004692 metal hydroxides Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000002203 pretreatment Methods 0.000 claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 6
- 239000008158 vegetable oil Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 230000002452 interceptive effect Effects 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000012071 phase Substances 0.000 description 46
- 230000000052 comparative effect Effects 0.000 description 13
- 235000019197 fats Nutrition 0.000 description 12
- 235000019484 Rapeseed oil Nutrition 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000010868 animal carcass Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000003225 biodiesel Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 235000021184 main course Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/06—Refining fats or fatty oils by chemical reaction with bases
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19925871A DE19925871A1 (de) | 1999-06-07 | 1999-06-07 | Verfahren zur Herstellung von Fettsäureestern einwertiger Alkylalkohole und deren Verwendung |
PCT/EP2000/005255 WO2000075098A1 (de) | 1999-06-07 | 2000-06-07 | Verfahren zur herstellung von fettsäureestern einwertiger alkylalkohole und deren verwendung |
Publications (2)
Publication Number | Publication Date |
---|---|
PL352527A1 PL352527A1 (en) | 2003-08-25 |
PL205257B1 true PL205257B1 (pl) | 2010-03-31 |
Family
ID=7910398
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL352527A PL205257B1 (pl) | 1999-06-07 | 2000-06-07 | Sposób wytwarzania estrów kwasów tłuszczowych z jednowodorotlenowymi alkoholami alkilowymi oraz sposób wytwarzania paliwa do silników wysokoprężnych |
Country Status (12)
Country | Link |
---|---|
US (1) | US6538146B2 (cs) |
EP (1) | EP1183225B1 (cs) |
AT (1) | ATE248798T1 (cs) |
AU (1) | AU5812500A (cs) |
CZ (1) | CZ297802B6 (cs) |
DE (2) | DE19925871A1 (cs) |
EA (1) | EA004051B1 (cs) |
ES (1) | ES2206267T3 (cs) |
HU (1) | HUP0201656A3 (cs) |
PL (1) | PL205257B1 (cs) |
PT (1) | PT1183225E (cs) |
WO (1) | WO2000075098A1 (cs) |
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AU2002217070B2 (en) | 2000-12-04 | 2005-10-13 | Westfalia Separator Ag | Method for the production of fatty acid esters |
DE10138822A1 (de) * | 2001-08-14 | 2003-03-06 | Bruno Berger | Umesterungsvorrichtung mit Schrägrohrreaktor |
AU2002347198B2 (en) * | 2001-12-13 | 2008-04-17 | Jott Australia Pty Ltd | Process for production of fatty acid esters |
DE10210432A1 (de) * | 2002-03-09 | 2003-09-18 | Dracowo Forschungs Und Entwick | Verfahren zur kontinuierlichen Herstellung von Biomethanoldiesel |
DE10241659A1 (de) * | 2002-09-05 | 2004-03-25 | Oliver Riess | Flüssiger Kraftstoff und Verfahren zu seiner Herstellung |
US7387712B2 (en) | 2002-10-17 | 2008-06-17 | Carnegie Mellon University | Catalytic process for the treatment of organic compounds |
US7157401B2 (en) | 2002-10-17 | 2007-01-02 | Carnegie Mellon University | Catalyst for the treatment of organic compounds |
US7871448B2 (en) | 2003-01-27 | 2011-01-18 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US7806945B2 (en) * | 2003-01-27 | 2010-10-05 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US9725397B2 (en) | 2003-01-27 | 2017-08-08 | REG Seneca, LLC | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US8088183B2 (en) * | 2003-01-27 | 2012-01-03 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
WO2005035693A2 (en) | 2003-10-02 | 2005-04-21 | Mississippi State University | Production of biodiesel and other valuable chemicals from waste water treatment plant sludges |
US20050274065A1 (en) * | 2004-06-15 | 2005-12-15 | Carnegie Mellon University | Methods for producing biodiesel |
BRPI0615085A2 (pt) * | 2005-08-25 | 2011-06-28 | Solix Biofuels Inc | método, aparelho, e sistema para produção de biodiesel a partir de alga |
US20080113067A1 (en) * | 2005-10-17 | 2008-05-15 | Monoj Sarma | Protein-Containing Food Product and Coating for a Food Product and Method of Making Same |
US20070087085A1 (en) * | 2005-10-17 | 2007-04-19 | Bunge Oils, Inc. | Protein-containing food product and coating for a food product and method of making same |
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US8445709B2 (en) * | 2006-08-04 | 2013-05-21 | Mcneff Research Consultants, Inc. | Systems and methods for refining alkyl ester compositions |
US7897798B2 (en) * | 2006-08-04 | 2011-03-01 | Mcneff Research Consultants, Inc. | Methods and apparatus for producing alkyl esters from lipid feed stocks and systems including same |
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DE102006044467B4 (de) * | 2006-09-21 | 2008-07-17 | Lurgi Gmbh | Verfahren zur kontinuierlichen Herstellung von Fettsäure-Methylester oder Fettsäure-Ethylester |
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US8017796B2 (en) * | 2007-02-13 | 2011-09-13 | Mcneff Research Consultants, Inc. | Systems for selective removal of contaminants from a composition and methods of regenerating the same |
US8148120B2 (en) * | 2007-03-28 | 2012-04-03 | Clemson University Research Foundation | Concentration and separation of lipids from renewable resources |
DE102007016157A1 (de) | 2007-04-02 | 2008-10-09 | Bayer Technology Services Gmbh | Verfahren zur Trennung von Produktgemischen aus Umesterungsreaktionen |
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US9328054B1 (en) | 2013-09-27 | 2016-05-03 | Travis Danner | Method of alcoholisis of fatty acids and fatty acid gyicerides |
US10239812B2 (en) | 2017-04-27 | 2019-03-26 | Sartec Corporation | Systems and methods for synthesis of phenolics and ketones |
US10696923B2 (en) | 2018-02-07 | 2020-06-30 | Sartec Corporation | Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids |
US10544381B2 (en) | 2018-02-07 | 2020-01-28 | Sartec Corporation | Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid |
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-
1999
- 1999-06-07 DE DE19925871A patent/DE19925871A1/de not_active Ceased
-
2000
- 2000-06-07 EP EP00943778A patent/EP1183225B1/de not_active Expired - Lifetime
- 2000-06-07 WO PCT/EP2000/005255 patent/WO2000075098A1/de active IP Right Grant
- 2000-06-07 EA EA200101267A patent/EA004051B1/ru not_active IP Right Cessation
- 2000-06-07 AT AT00943778T patent/ATE248798T1/de not_active IP Right Cessation
- 2000-06-07 AU AU58125/00A patent/AU5812500A/en not_active Abandoned
- 2000-06-07 HU HU0201656A patent/HUP0201656A3/hu unknown
- 2000-06-07 ES ES00943778T patent/ES2206267T3/es not_active Expired - Lifetime
- 2000-06-07 PL PL352527A patent/PL205257B1/pl not_active IP Right Cessation
- 2000-06-07 DE DE50003549T patent/DE50003549D1/de not_active Expired - Lifetime
- 2000-06-07 CZ CZ20014388A patent/CZ297802B6/cs not_active IP Right Cessation
- 2000-06-07 PT PT00943778T patent/PT1183225E/pt unknown
-
2001
- 2001-12-07 US US10/012,811 patent/US6538146B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
AU5812500A (en) | 2000-12-28 |
PT1183225E (pt) | 2004-01-30 |
WO2000075098A1 (de) | 2000-12-14 |
PL352527A1 (en) | 2003-08-25 |
HUP0201656A2 (en) | 2002-09-28 |
EA200101267A1 (ru) | 2002-06-27 |
EA004051B1 (ru) | 2003-12-25 |
DE50003549D1 (de) | 2003-10-09 |
DE19925871A1 (de) | 2000-12-21 |
ES2206267T3 (es) | 2004-05-16 |
CZ20014388A3 (cs) | 2002-05-15 |
EP1183225A1 (de) | 2002-03-06 |
HUP0201656A3 (en) | 2003-08-28 |
US20020156305A1 (en) | 2002-10-24 |
ATE248798T1 (de) | 2003-09-15 |
EP1183225B1 (de) | 2003-09-03 |
CZ297802B6 (cs) | 2007-04-04 |
US6538146B2 (en) | 2003-03-25 |
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Legal Events
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LAPS | Decisions on the lapse of the protection rights |
Effective date: 20100607 |